2-(4-(adaMantan-1-yl)phenoxy)acetic acid Chemical Properties

Melting point:

168-170℃ (acetic acid water )

Boiling point:

441.1±28.0 °C(Predicted)

Density 

1.226±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.21±0.10(Predicted)

Appearance

White to off-white Solid

2-(4-(adaMantan-1-yl)phenoxy)acetic acid Usage And Synthesis

Synthesis

LiOH-H2O (0.29 g, 7.00 mmol) was added to a solution of 2-(4-(1-adamantyl)phenoxy)ethyl acetate (1.10 g, 3.50 mmol) in THF/H2O (1:1, 20.0 mL). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, it was acidified with 10% HCl solution to pH 2. The organic layer was separated by adding EtOAc for extraction. After concentration of the organic phase, the residue was purified by silica gel column chromatography (eluent: CH2Cl2/MeOH = 30:1) to afford 2-(4-(1-adamantyl)phenoxy)acetic acid as a white solid (0.61 g, 61.3% yield).1H NMR (CDCl3, 500 MHz) δ 7.29 (d, 2H, J = 6.75 Hz, Ar-H), 6.87 (d, 2H, Ar-H), 6.87 (d, 2H, J = 6.75 Hz, Ar-H), 7.29 (d, 2H, J = 6.75 Hz, Ar-H). 6.87 (d, 2H, J = 6.74 Hz, Ar-H), 4.61 (s, 2H, -OCH2COO-), 2.04 (s, 4H, adamantyl), 1.86 (m, 6H, adamantyl), 1.76 (m, 6H, adamantyl); 13C NMR (CDCl3, 125 MHz) δ 156.16, 142.71, 127.35, 114.31, 64.21, 42.51, 36.84, 36.17, 28.16; LCMS m/z calculated value (MH+) 287.16, measured value 287.26.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6305 - 6310
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1675 - 1684
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7456 - 7460
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1453 - 1456
[5] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 12, p. 3826 - 3829

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